Reactions

Alkene halogenation

Abstract

Alkene halogenation is a reaction in which a dihalogen (typically Br2 or Cl2) adds across the double bond of an alkene, yielding a vicinal dihalide, where one halogen atom is added to each carbon of the former double bond.

General reaction scheme of Alkene halogenation

Keywords

Alkene, Alkyl dihalide


Category

Alkene

Mechanism

First, 𝜋 electrons of the alkene act as nucleophile and attack one of the halogen atoms of the dihalogen, polarizing the X-X bond and resulting in the departure of a halide ion.The first halogen atom bridges the two carbons of the former double bond, forming a cyclic halonium ion. Subsequently, the halide ion attacks one of the two carbons of the halonium ion from the back side, generating the corresponding vicinal dihalide in an anti configuration.

Chemical mechanism of: Alkene halogenation